She formed a relationship with jazz pianist Bob Kelly, and they moved to London in 1955.[3] On MacGregor's recommendation, she was signed by Topic Records and, although reluctant to surrender her reputation as a solo performer, was persuaded to join the Chas McDevitt Skiffle Group to record Elizabeth Cotten's song "Freight Train".[1] The group had already recorded the song, with McDevitt singing, but re-recorded it with Nancy Whiskey's vocals.[3] The record made the top five in the UK Singles Chart in 1957, and she also toured the United States with McDevitt’s group and appeared on the Ed Sullivan Show.[3] "Freight Train" sold over one million copies, and was awarded a gold disc.[4] A dispute over the rights to the song, which had been introduced to Britain by Peggy Seeger, was eventually settled out of court.[3]

After a second, smaller hit, "Greenback Dollar", Whiskey left the group. She disliked the skiffle style which she was obliged to perform with McDevitt, and her outspoken comments, together with the fact that she was expecting a child with Bob Kelly, a married man, offended some fans.[1] She resumed a solo career and - after his divorce - married Kelly, who became a member of her backing group, the Skifflers, who later renamed themselves as the Teetotallers. She also recorded several singles for Oriole Records in the late 1950s, and released an album, The Intoxicating Miss Whiskey.[3]

She and Kelly moved to Melton Mowbray, Leicestershire, around 1958 after the birth of their daughter (named Yancey Anne in tribute to pianist Jimmy Yancey). Although by the 1970s she had largely retired from the mainstream music industry, she continued to perform occasionally in folk clubs, and at other events such as a 1997 gala concert at the Royal Albert Hall billed as "The Roots Of British Rock".[3]